Diastereoselective Synthesis of Symmetrical and Unsymmetrical Tetrahydropyridines Catalyzed by Bi(III) Immobilized on Triazine Dendrimer Stabilized Magnetic Nanoparticles

Abstract

Unsymmetrical 1,2,5,6-tetrahydropyridine-3-carboxylates were obtained for the first time from a five-component FeO@TDSN-Bi(III)-catalyzed reaction of aryl aldehydes, aryl amines, and ethyl acetoacetate. This magnetically separable catalyst enabled the selective incorporation of two different aryl amines or two different aryl aldehydes into the product, and provided excellent yields, short reaction times, mild reaction conditions, satisfactory catalyst recyclability, and low catalyst loading.

Efficient and Eco‐Friendly One‐Pot Synthesis of Functionalized Furan‐2‐one, Pyrrol‐2‐one, and Tetrahydropyridine Using Lemon Juice as a Biodegradable Catalyst

“…have been used for the construction of THPD ring. Recently, anionic surfactants sodium dioctylsulfosuccinate (SDOSS), Calix[n]arenes, ethylenediammoniumdiformate (EDDF), cyanuric acid, graphene oxide, polyphosphoric acid supported on silica‐coated magnetic nanoparticles and Bi(III) immobilized on triazine dendrimer stabilized magnetic nanoparticles (Fe 3 O 4 @TDSN−Bi(III)) have been utilized to synthesize this six‐membered nitrogen containing compound. Last year, we published a review article, which uncovered various synthetic strategies developed in the past decade for manufacturing THPD compounds …”

Recent Developments on Five-Component Reactions

“…There are several papers on the synthesis of piperidine derivatives through the reaction of aromatic aldehydes, anilines, and β-keto esters under different conditions. Catalysts used for the reactions include acetic acid [60], ethylenediammonium diformate (EDDF) [61], nanostructured PbCr x Fe 12−x O 19 [62], Fe 3 O 4 @TDSN-Bi(III) [63], anionic surfactants sodium dioctyl sulfosuccinate (SDOSS), and sodium dodecyl sulfate (SDS) [64].…”

One‐Pot Pseudo Five Component Synthesis of Biologically Relevant 1,2,6‐Triaryl‐4‐arylamino‐piperidine‐3‐ene‐3‐ carboxylates: A Decade Update

“…The same synthesized compounds were also screened for their anti‐cancer and free radical scavenging activity . Very recently, in 2017, Asadi et al . successfully immobilized Bi(III) on nano‐Fe 3 O 4 supported triazine dendrimer [Fe 3 O 4 @TD−Bi(III)].…”

“…[25] The same synthesized compounds were also screened for their anti-cancer and free radical scavenging activity. [26] Very recently, in 2017, Asadi et al [43] successfully immobilized Bi(III) on nano-Fe 3 O 4 supported triazine dendrimer [Fe 3 O 4 @TDÀ Bi(III)]. Using this nano-material as catalyst they synthesized a series of functionalized piperidines with excellent yields in ethanol within just three hours at room temperature (Scheme 8).…”